PRODUCTS

ISOBUTYRIC ACID

CAS NUMBER: 79-31-2

EC NUMBER: 201-195-7

MOLECULAR FORMULA: (CH3)2CHCOOH

MOLECULAR WEIGHT: 88.11

IUPAC NAME: 2-methylpropanoic acid

Isobutyric Acid, also known as 2-methylpropanoic acid or isobutanoic acid, is a carboxylic acid with structural formula (CH3)2CHCOOH.
Isobutyric Acid is an isomer of n-butyric acid.
Isobutyric Acid is classified as a short-chain fatty acid.
Deprotonation or esterification gives derivatives called isobutyrates.

Isobutyric Acid appears as a colorless liquid with a light odor of rancid butter.
Isobutyric Acid is Corrosive to metals and tissue.
Isobutyric Acid is a branched fatty acid comprising propanoic acid carrying a methyl branch at C-2.

Isobutyric Acid has a role as a volatile oil component, a plant metabolite and a Daphnia magna metabolite.
Isobutyric Acid is a branched-chain saturated fatty acid, a methyl-branched fatty acid and a fatty acid 4:0.
Isobutyric Acid is a conjugate acid of an isobutyrate.

Isobutyric Acid is a colorless liquid with a somewhat unpleasant odor.
Isobutyric Acid is soluble in water and organic solvents.
Isobutyric Acid is found naturally in carobs (Ceratonia siliqua), in vanilla, and in the root of Arnica dulcis, and as an ethyl ester in croton oil

Production:
Isobutyric Acid is manufactured by the oxidation of isobutyraldehyde, which is a byproduct of the hydroformylation of propylene.
Isobutyric Acid can also be prepared by the high pressure hydrocarboxylation (Koch reaction) from propylene:
CH3CH=CH2 + CO + H2O → (CH3)2CHCO2H

Isobutyric Acid can also be manufactured commercially using engineered bacteria with a sugar feedstock.

Laboratory Methods:
Many routes are known including the hydrolysis of isobutyronitrile with alkalis and the oxidation of isobutanol with potassium dichromate in the presence of sulfuric acid.
In the presence of proton donors, the action of sodium amalgam on methacrylic acid also gives isobutyric acid.

Reactions:
The acid reacts as a typical carboxylic acid:
Isobutyric Acid can form amide, ester, anhydride, and chloride derivatives.
Isobutyric Acid's acid chloride is commonly used as the intermediate to obtain the others.
When heated with a chromic acid solution it is oxidized to acetone.
Alkaline potassium permanganate oxidizes it to α-hydroxyisobutyric acid, (CH3)2C(OH)-CO2H.

Uses of Isobutyric Acid:
Isobutyric acid and its volatile esters are present naturally in a wide variety of foods and, at varying concentrations, can impart a range of flavors.
The compound's safety as a food additive was reviewed by an FAO and WHO panel, who concluded that there were no concerns at the likely levels of intake

Biology of Isobutyric Acid:
In humans, isobutyric acid is a minor product of the gut microbiome and can also be produced by metabolism of its esters found in food.
Isobutyric Acid has a characteristic odor like rancid butter (4-carbon organic compounds take the root, butyl, which is in turn from butyric which is in turn from the Latin word for butter and the Greek, βούτυρον) but anosmia for it has been reported in about 2.5% of people.

APPLICATIONS OF ISOBUTYRIC ACID:

-Baked goods

-Chewing gum

-Fats

-oils

-Frozen dairy

-Gelatins

-puddings

-Hard candy

-Milk products

-Nonalcoholic beverages

-Soft candy

-Sweet sauce

*Agriculture intermediates
*Dyes / pigments / paints
*Food flavors & food fragrances
*Fragrance ingredients
*Herbicides - intermediate for other
*Intermediates
*Other-food chemicals
*Pharmaceutical chemicals
*Protective coatings

Isobutyric acid is a carboxylic or short chain fatty acid with characteristic sweat-like smell. Small amount of isobutyrate is generated via microbial (gut) metabolism.
Small amounts may also be found in certain foods or fermented beverages.
There is anosmia (genetic inability to smell) for the odor of isobutyric acid with a frequency of about 2.5%. (OMIM 207000 ).
Isobutyric acid is slightly soluble in water but much more soluble in ethanol, ether and organic solvents.
Isobutyric acid can affect people if breathed in and may be absorbed through the skin.
Contact can irritate and burn the skin and eyes.
Breathing Isobutyric acid can irritate the nose, throat and lungs causing coughing, wheezing and/or shortness of breath.

Alternative Classes:
-Monocarboxylic acids and derivatives
-Organic oxides
-Hydrocarbon derivatives
-Carbonyl compounds

Substituents:
-Monocarboxylic acid or derivatives
-Carboxylic acid
-Organic oxygen compound
-Organic oxide
-Hydrocarbon derivative
-Organooxygen compound
-Carbonyl group
-Aliphatic acyclic compound

Esters of isobutyric acid are used as solvents for various applications where desirable odors and flavor characteristics are important.
The potassium salt of isobutyric acid is effective as a solubility promoter in the caustic extraction of mercaptans from sour petroleum stocks.

Isobutyric acid is mainly used in the synthesis of isobutyric acid esters, such as:
-methyl isobutyrate
-propyl ester
-isoamyl ester
-benzyl ester

Isobutyric Acid can also be used as edible flavor and used in pharmaceutical.
GB 2760-1996 provides for isobutyric acid as the food flavors allowed to use.
Isobutyric Acid is mainly used for the preparation of:
-butter
-apple
-caramel
-cheese
-bread
-yeast
-flavors

Isobutyric Acid is not more important than butyric acid, but has the similar uses with n-butyric acid.
Isobutyric Acid is mainly used to produce the corresponding esters, such as:
-methyl isobutyrate with apricot incense
-propyl isobutyrate with pineapple flavor
-isobutyl isobutyrate with banana flavor
-octyl isobutyrate with grapes taste
-benzyl isobutyrate with jasmine smell, etc.

Isobutyric Acid can be used for preparing flavors and solvents and also used in the manufacture of varnishes and plasticizers.
Isobutyric Acid has some important derivatives that, in the industry, is actually used for the production of isobutyronitrile intermediates, and then converted to isobutylamidine hydrochloride that is the raw materials of pesticide diazinon.
Isobutyric Acid is used for the raw materials of perfume and perfume ester, and also used as the solvents of textile auxiliaries (in the form of salt) and a variety of chemical reactions.

Production Method:
The preparation of Isobutyric Acid is similar with butyric acid, which is performed by the direct oxidation of isobutyl alcohol and isobutyraldehyde.
Isobutyric Acid can be directly generated from the oxidation of isobutyraldehyde in air or oxygen.
Other manufacturing methods have isobutyronitrile hydrolysis and methacrylic acid hydrogenation.
The oxidation of 2-methyl-1-nitropropane to prepare isobutyric acid can also obtain a higher yield.
The purification of Isobutyric acid can be realized by azeotropic distillation with water, and anhydrous isobutyric acid can be obtained by the extractive distillation from carbon tetrachloride.
Propylene and formic acid ester can react at 50 °C with the catalysis of hydrofluoric acid to generate methyl isobutyrate and propyl isobutyrate.

Applications of Isobutyric Acid:
Isobutyric Acid is not more important than butyric acid, but has the similar uses with n-butyric acid.
Isobutyric Acid is mainly used to produce the corresponding esters, such as methyl isobutyrate with apricot incense, propyl isobutyrate with pineapple flavor, isobutyl isobutyrate with banana flavor, octyl isobutyrate with grapes taste, benzyl isobutyrate with jasmine smell, etc.
Isobutyric Acid can be used for preparing flavors and solvents and also used in the manufacture of varnishes and plasticizers.
Isobutyric Acid has some important derivatives that, in the industry, is actually used for the production of isobutyronitrile intermediates, and then converted to isobutylamidine hydrochloride that is the raw materials of pesticide diazinon.

Isobutyric Acid has an odor and flavor similar to n-butyric acid.
Prepared via oxidation of isobutyl alcohol.
Isobutyric Acid has strong penetrating odor of rancid butter.
The odor and flavor are similar to n-butyric acid

Isobutyric Acid is used to prepare esters for flavors and perfumes.
Isobutyric Acid is also used as a disinfecting agent, preservative and tanning agent.
Isobutyric Acid finds applications in textile, varnish and the leather industry.
Further, it is used as a lactation stimulant in dairy cattle.
In addition to this, it is used in the preparation of tetramethylsuccinic acid and diisopropyl ketone.

Isobutyric Acid is a flavoring agent that is a colorless liquid with a strong, penetrating odor, resembling butter.
Isobutyric Acid is miscible in alcohol, propylene glycol, glycerin, mineral oil, and most fixed oils and sol- uble in water.
Isobutyric Acid is obtained by chemical synthesis.
Isobutyric Acid is also termed isopropylformic acid.

PHYSICAL PROPERTIES OF ISOBUTYRIC ACID:

-Molecular Weight: 88.11

-XLogP3-AA: 0.8

-Exact Mass: 88.052429494

-Monoisotopic Mass: 88.052429494

-Topological Polar Surface Area: 37.3 Å²

-Physical Description: colourless liquid with a strong penetrating odour of rancid butter

-Color: Colorless

-Form: liquid

-Odor: Pungent odor like that of butyric acid, but not as unpleasant

-Taste: CHEESY TASTE

-Boiling Point: 154.4 °C

-Melting Point: -46 °C

-Flash Point: 56 °C

-Solubility: 1.90 M

-Density: 0.950

-Vapor Density: 3.0

-Vapor Pressure: 1.81 mmHg

-Stability/Shelf Life: Stable during transport

-Autoignition Temperature: 481 °C

-Decomposition: When heated to decomposition it emits acrid smoke and fumes

-Viscosity: 1.126 mPa.s

-Corrosivity: It is corrosive to metals

-Heat of Vaporization: 11,182.8 g cal/g mole

-Surface Tension: 24.4mN/m

-Odor detection threshold in water: 8.1 ppm

CHEMICAL PROPERTIES OF ISOBUTYRIC ACID:

-Heavy Atom Count: 6

-Formal Charge: 0

-Complexity: 56.6

-Isotope Atom Count: 0

-Defined Atom Stereocenter Count: 0

-Undefined Atom Stereocenter Count: 0

-Defined Bond Stereocenter Count: 0

-Undefined Bond Stereocenter Count: 0

-Covalently-Bonded Unit Count: 1

-Compound Is Canonicalized: Yes

-Hydrogen Bond Donor Count: 1

-Hydrogen Bond Acceptor Count: 2

-Rotatable Bond Count: 1

-Index of refraction: 1.3930 at 20 °C/D

-pKa: 4.84

-LogP: 0.94

-LogS: 0.28

-Henrys Law Constant: 8.85e-07 atm-m3/mole

-Atmospheric OH Rate Constant: 2.00e-12 cm3/molecule*sec

STORAGE OF ISOBUTYRIC ACID:

Isobutyric Acid should be stored at +4°C
Isobutyric Acid should be stored in a cool environment.
Isobutyric Acid should be stored in a dry place.
Isobutyric Acid can be easily stored as it is suitable for air transportation.

Isobutyric Acid should be stored in a regularly ventilated place.
Isobutyric Acid should be kept tightly closed.

Isobutyric Acid should not be stored together with strong bases.
Isobutyric Acid should be stored under constant pressure.

Isobutyric Acid should be stored at a constant temperature.
Isobutyric Acid should be stored in a place where there are no sudden temperature changes.
Isobutyric Acid should be stored in a moisture-free and dry place.

SYNONYMS:

2-Methylpropanoic acid
Isobutanoic acid
2-Methylpropionic acid
Propanoic acid, 2-methyl-
Dimethylacetic acid
Isopropylformic acid
Iso-butyric acid
Isobutyrate
Cenex RP b2
alpha-Methylpropanoic acid
alpha-Methylpropionic acid
Acetic acid, dimethyl-
Isobutanoate
Propionic acid, 2-methyl-
2-METHYL-PROPIONIC ACID
Isobutyric acid (natural)
Tenox IBP-2
2-Methylpropanoate
Kyselina isomaselna
Kyselina isomaselna [Czech]
iso-C3H7COOH
Isobuttersaeure
i-Butyric acid
Methylpropanoic acid, 2-
Tenox IBP-2 Grain Pr.
methylpropanoic acid
alpha-isobutyric acid
2-methyl-propanoic acid
2,2-dimethylacetic acid
.alpha.-Methylpropanoic acid
.alpha.-Methylpropionic acid
Dimethylacetate
i-butyrate
iso-Butyrate
a-Methylpropanoate
a-Methylpropionate
1iup
methylpropionic acid
Isobutyric-d6 Acid
2-Methylpropionsaeure
alpha-Methylpropanoate
alpha-Methylpropionate
a-Methylpropanoic acid
a-Methylpropionic acid
Isobutyric acid, 99%
2-methyl propanoic acid
2-Propanecarboxylic acid
isopropyl carboxylic acid
4-02-00-00843 (Beilstein Handbook Reference)
2-Methyl Propionic Acic, Natural
Isobutyric acid, analytical standard
Isobutyric acid, >=99%, FCC, FG
Isobutyric acid, puriss. p.a., >=99.5%
Isobutyric acid, natural, >=99%, FCC, FG
Isobutyric acid, certified reference material, TraceCERT(R)
2-Methyl-d3-propionic-3,3,3-d3 acid;[2H6]-2-Methylpropionic acid